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Mass Spectrometry pp 207–257Cite as

Cannabinoids

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Part of the book series: Modern Analytical Chemistry ((MOAC))

Abstract

The cannabinoids form a group of terpene-related compounds unique to the plant Cannabis sativa L., the source of the drug marijuana. To date, some 70 of these compounds have been identified (1), the major ones having the structures shown in Fig. 6.1. Of these, delta-9-tetrahydrocannabinol (delta-9-THC, I) is the major psychoactive constituent, cannabidiol (CBD, II) is its biosynthetic precursor, and cannabinol (CBN, III) is generally regarded as a chemical degradation product (2). Most of the major cannabinoids possess a pentyl chain, but the complexity of cannabinoid mixtures arises from the presence of lower homologues, of which the propyl series is the best known (3). Methyl (4) and butyl (5) cannabinoids have also been reported, but in low concentration. An interesting feature of the relative abundance of all of the cannabinoids is their dependence on geographical origin and age. Plants grown in temperate regions tend to have low THC contents, whereas those originating in tropical regions contain high concentrations of this cannabinoid. In addition, the relative concentration of the homologues displays a strong regional bias with, for example, propyl cannabinoids being particularly abundant in samples originating from the Indian subcontinent. Further complexity is imparted by the fact that most natural cannabinoids contain a carboxylic acid group either at C-2 (named acid A, IV) or at C-4 (acid B, V). This group is labile, is lost when the drug is smoked, and presents problems when analysis is performed by gas chromatography.

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  1. Department of Pharmacology, University of Oxford, Oxford, OX1 3QT, England

    David J. Harvey

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  1. Departments of Neurology and Biochemistry, The University of Tennessee, Memphis, Memphis, Tennessee, USA

    Dominic M. Desiderio

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Harvey, D.J. (1992). Cannabinoids. In: Desiderio, D.M. (eds) Mass Spectrometry. Modern Analytical Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1173-5_6

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